Methanol → HCID 67830065, compound

HRID 2081739Notes

Reaction equation

HRID 2081739 reaction equation
[CH:1](=[N:8][N:9]1[CH2:13][CH2:12][N:11]([C@@:14]2([C:32]([O:34][CH:35]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:33])[S:20][C@H:19]3[N:16]([C:17](=[O:31])[C@H:18]3[NH:21]C(=O)CC3C=CC=CC=3)[CH2:15]2)[C:10]1=[O:48])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)[Cl:59].CO>C(Cl)Cl.C(OCC)(=O)C>[ClH:59].[NH2:21][C@@H:18]1[C:17](=[O:31])[N:16]2[C@@H:19]1[S:20][C@@:14]([N:11]1[CH2:12][CH2:13][N:9]([N:8]=[CH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:10]1=[O:48])([C:32]([O:34][CH:35]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)=[O:33])[CH2:15]2

Participants

7

Reactant 4

HCID 887MethanolHCID 949N,N-DimethylanilineHCID 24819Phosphorus pentachlorideHCID 54247171HCID 54247171, compound

Product 1

HCID 67830065HCID 67830065, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-60 °C

Procedure

In 664 ml of methylene chloride was dissolved 83.0 g of (3R,5R,6R)-3-(3-benzylideneamino-2-oxo-imidazolidin-1-yl)-3-diphenylmethyloxycarbonyl-7-oxo-6-phenylacetamido-4-thia-1-azabicyclo[3.2.0]heptane. The solution was cooled to -60° C. To the solution were added 55.8 ml of N,N-dimethylaniline and 39.3 g of phosphorus pentachloride in this order. The temperature of the mixture was elevated to -20° C. in 30 minutes and then recooled to -60° C. To the reaction mixture was added 66.3 ml of anhydrous methanol, and the mixture was heated to 0° C. in 30 minutes and stirred at the same temperature for 30 minutes. 664 ml of ethyl acetate was added to the reaction mixture. The mixture was stirred for 15 minutes with ice cooling. The resulting crystals were collected by filtration, washed twice each with 83 ml of methylene chloride and once with 83 ml of ethyl acetate, and dried under reduced pressure to obtain 57.5 g (yield: 79.0%) of (3R,5R,6R)-6-amino-3-(3-benzylideneamino-2-oxoimidazolidin-1-yl)-3-diphenylmethyloxycarbonyl-7-oxo-4-thia-1-azabicyclo[3.2.0] heptane hydrochloride.

Workup

  1. customrecooled to -60° C
  2. temperaturethe mixture was heated to 0° C. in 30 minutes
  3. stirringThe mixture was stirred for 15 minutes with ice cooling
  4. filtrationThe resulting crystals were collected by filtration
  5. washwashed twice each with 83 ml of methylene chloride
  6. dry with materialonce with 83 ml of ethyl acetate, and dried under reduced pressure

Sources & evidence

ORD record
ord-e9f77244fe19452b9284db24c1e67dd4
Source dataset
uspto-grants-1993_02
Patent number
US05185330

Reaction notes

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